


Pretty For You

by anemptymargin



Category: Critical Role (Web Series) RPF
Genre: Crossdressing Kink, Feminization, Kink Meme, M/M, Makeup
Language: English
Status: In-Progress
Published: 2017-07-04
Updated: 2017-07-04
Packaged: 2018-11-23 04:42:28
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 3,552
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/11395566
Author URL: https://archiveofourown.org/users/anemptymargin/pseuds/anemptymargin
Summary: It's something he's never really done with anyone, it's never been something he needs, but when Matt gets a chance to explore his feminine side with someone he loves and trusts, it's amazing.





	1. Something Discovered

**Author's Note:**

> Please, please don't share this with the cast/crew. This is for my own filthy mind and those of others in my palatial gutter. Don't like? Don't read.

It started small and simple, nail polish or wraps that went from more gender neutral black or greens to a glittery pink that made Marisha giggle, testing the waters.

 

“Yeah, if that's what you like, you do you?” She never questioned him, not even when she caught him hiding a pair of impressive baby pink stilettos. “I mean, it doesn't really do anything for me, but if you want to dress up, I won't judge you. I love you, baby. You know that.”

 

He put them away. He didn't have to have them, didn't have to feel pretty when there were a thousand other things that worked for both of them.

 

Then there was Taliesin. Taliesin who had always been there, who was now even more there. In their home, in their bed. And now, in their closet helping them pack for the big move.

 

“Oh, hello…” Taliesin cooed, tipping the top of the box to peek at the shoes that were too large to have been Marisha’s and had been tucked under half a chainmail shirt. “I assume these are coming?” He tilted his head back to where Matt stared at him from his spot on the bed.

 

Like a deer in the headlights, Matt was unmoving for a long moment. In a reedy and surprised tone, he answered; “I… ah… no. I should probably donate them.”

 

Taliesin barely frowned and wrapped his fingers around the heel, drawing it out of the box and turning it over in his hand. They were immaculate, maybe worn once. There was a story there he wanted to know. “If you don't mind, I'd like to hold on to them.”

 

“What?” Matt’s voice came out a panicked yelp. “Why?”

 

Taliesin shrugged. “Never know when a pair of shoes will come in handy.”

 

Matt swallowed hard, watching wide-eyed at the reverence Taliesin handled them with as he carefully tucked them back into the box and folded lilac tissue paper over their fabric exterior. “Never really pictured you in pink.”

 

“Oh god no.” Taliesin laughed, his cheeks warming. “It's much more your color.” He turned to lean his shoulder against the bed, peering over the edge to see Matt’s flushed cheeks and red ears. “Have you got the outfit they go with?”

 

Matt blushed darker and ducked his head slightly, a sheaf of hair falling into his face. Taliesin assumed that was the only answer he’d get and closed the lid, setting the box aside before a much softer voice escaped Matt’s throat. “I never bought one. I didn’t… it’s… it’s silly.”

 

“Dancing shoes, never worn. How very Hemingway of you.” Taliesin sighed, letting the words tickle over his brain in Matt’s almost defeated tone. It was obvious what the situation was; he’d known Matt long enough to know both that a certain degree of gender non-conformity wasn’t really shocking and that he was quite likely to simply ignore urges that his romantic partner didn’t enjoy. “She doesn’t like it, then?”

 

Matt’s weight shifted toward the edge of the bed when Taliesin looked back up at him. Whispering as though they’d be overheard, he answered; “‘It’s not her thing. No big deal, like I said.”

 

Taliesin frowned again and turned his body before pushing up onto his knees and leaning his elbows on the bed to assault Matthew with a tender gaze. “And now… she’s not the only lover in your life.”

 

Matt’s brow furrowed as he considered what Taliesin was offering, and clearly he was. “Are you saying that you want me to dress up for you?”

 

His lips curled into a much wider wicked smile. “I’d love if you dressed up for me.”

 

A small whine closed Matt’s throat and he crossed his arms over his chest. He hadn’t even thought about it, well… since the last time he’d had to move that box to shove something else into his side of the closet. He’d never considered that that Taliesin would want that… though, in fairness it made a lot of sense for him. “You sure you don’t want to dress up instead?”

 

“I might,” he purred in response, “But for now I’d like to see what those special heels inspire.”


	2. Chapter 2

It was Taliesin who had to push Matt further, and he knew it. Matt didn't want to feel like he was pushing something  _ weird _ on someone else, even though it wasn't really weird at all. Actually, for Taliesin’s sensibilities, it was quite nice.

 

Once they had started settling in, Taliesin spent a lot of time at the new place helping out in both physical labor and happy fun time. It was in that small slice of a few weeks that he finally found time to be alone with Matt and lure him away from the dozens of projects he was working on. 

 

“Hey,  come here for a sec!” Taliesin called from the futon spread out on the living room floor.

 

Matt grumbled something from the office, but eventually made it over in his pajama pants and t-shirt. “Yeah? What’s up?”

 

“Break time,” Taliesin stated simply, reaching up to take Matt’s hand and guide him down to join him. “I’ve brought something for you.”

 

An eyebrow cocked, but Matt said nothing as a black zippered bag was opened. He leaned to look inside only to have Taliesin’s arm snake around his waist and pull him in closer.

 

“In my lap,” Taliesin grunted, a grin stretching his lips when Matt accepted without argument, opening his knees to straddle Taliesin’s thick thighs until they were pressed belly to belly.

 

On reflex, Matt curled inward and pressed his face into Taliesin’s shoulder, arms wrapping around him comfortably. It was the casual sort of affection they shared long before they were physically intimate, now layered with that extra stirring of potential arousal. It was easy with him, easy to let go and just enjoy the touch.

 

Taliesin stilled his intent picking through the bag for a moment, taking the time to pat Matt’s back and rub a slow circle. “As much as I would love to cuddle you all afternoon, I think I have something a little more interesting to try.”

 

Lifting his head, Matt let out a small sleepy sound. “Huh?”

 

A quick shift was all it took to fish a soft pink lipstick out of the bag and hold it up where Matt could see. “I spent two hours last night at Sephora to get the products to recreate a tutorial. I’m pretty sure if I could make myself look like a prom queen, you’ll look amazing.”

 

Slowly, Matt’s lips curled into an excited smile and he wiggled in Taliesin’s generous lap, squeezing his arms around Tal’s middle. “Oh my god… I can’t believe-”

 

“Believe it,” Taliesin murmured against his ear and then brushed a fond kiss on Matt’s cheek. “Go wash your face and shave.”

 

Matt didn’t answer so much as explode off of Taliesin’s lap and lope to the bathroom. By the time he returned with his hair pulled into a high ponytail with one of Marisha’s scrunchies and dabbing the wetness off his face with a towel, Taliesin had lined up the products and re-watched the video just to be sure he had the right brushes and everything. The close shave and wash alone had left Matt’s face soft and slightly pink, the familiar scent of moisturizer clinging to his skin when he once more settled astride Taliesin's lap - further back than before to allow him to work. “Better?”

 

“Beautiful.” Taliesin smiled, unable to restrain himself from stealing a kiss. “Now, I’ll walk you through it, so next time you can do it yourself.”

 

A small excited sound closed Matt’s throat and he nodded eagerly. He’d only done camera and theater makeup, this was something different. Less focus on the dramatic aspects.

 

“Softness.” Taliesin whispered; “I got the impression you want something soft.”

 

Matt nodded only once and closed his eyes as Taliesin’s fingers began to stroke on thick liquid foundation. “Yes.”

 

“Foundation first, you may have to go a shade darker, but this works for today.” He applied the last swipe with his index finger and then began to gently blend and buff the liquid with a large brush. It was hard not to be distracted by the gentle flutter of Matt’s eyelashes and the small sighs that came with each tender brush stroke. The color was off, but not as bad as he’d originally anticipated. “Then, concealer. You’ve used this before for camera makeup, I know.” He didn’t need to go step by step through that, a small line patted gently to hide raccoon eyes and stress lines, and then smaller fine-tipped brush strokes to cover up the signs that Matt had ever dealt with the scourge of acne.

 

“Break.” Matt sighed when the brush stopped. He opened his eyes to offer another warm smile. “I’m not gonna lie here…” He grasped Taliesin’s hand forcing him to drop the next tube as it was guided to where Matt’s fleece pajama bottoms failed completely in hiding the tent of his arousal. “It’s going to be a little awkward dealing with makeup crew after this.”

 

Taliesin’s fingers wrapped around the shaft of Matt’s cock through the pants, offering a firm squeeze that drew out a moan from his lover’s chest. “Their interest is much different than mine,” he murmured; “I want to see my beautiful girl emerging, not cover up your minute imperfections for HD viewers.”

 

An obvious blush traced Matt’s throat from beneath his t-shirt collar and he shifted his hips against Taliesin’s touch only to have it draw away after a lingering moment. “I want to be beautiful.”

 

Taliesin took up a small brush once more, dipping it into highlighting concealer with an artist’s grace. “You are, darling.” He answered softly, Matt’s eyes closing when he began to make stripes around his eyes and mouth. “Without a single drop of makeup or high heeled shoe, you’re one of the single most beautiful people I know.” He sighed, taking up the foundation brush to gently pat out the contouring. “I just hope one day you’ll see it too.”

 

Awkward silence fell between them for a long moment, broken only by Taliesin’s careful narration of what he was doing. Eyebrow pencil, setting the foundation and contouring, a wide brush swiping shimmery pink blush across his cheeks. Priming eyelids, four different shadows.

 

“What kind of eye do you want, darling?” Taliesin cooed, already manipulating the liquid liner with no small amount of joy. It was something he used frequently enough to consider himself advanced in the application. “I was thinking a basic little swoop?”

 

“Anything,” Matt breathed, trying hard to remain still despite his mounting arousal with each tender stroke. “I trust you.”

 

Taliesin reached up to trace Matt’s shimmering eyelids, smudging the soft rose color with a thumb as he fought the tremor in his hand. Then, he removed the cap and without hesitating managed a flawless black top line, avoiding the bottom lid to make Matt’s eyes somehow seem even larger. A sweep of mascara across Matthew’s already long lashes, darkening them and adding a subtle curl. “You have anime eyes,” he whispered, “you’re going to love the way they turned out.”

 

The lips were last and Taliesin took his time there. The staff had been precious when he told them he was shopping for his boyfriend, something pink but not garish - soft and subtle, but highly feminine. What he ended up with was a Dior pink nude called Tease that cost far too much but swiped onto Matt’s soft lips with addicting ease. “Shall we see if it’s kiss-proof?” he murmured, capping the tube with a wicked smile as warm eyes opened to him once more. The makeup was complete, and almost eerie in how drastically twenty minutes of products had changed the landscape. Underneath it all, he was still Matt and the crooked grin wedged Taliesin’s way was proof of that. He reached up and tugged free the scrunchie, letting dark hair fall in waves to frame his perfect face, breath escaping his chest with a delighted groan.

 

Matt leaned into him, both hands sweeping across the freshly shaved sides of Taliesin’s head, gently raking along his scalp before joining at the back of his neck as Taliesin’s tongue darted over his lips and tasted the glossy pink lipstick.

 

When they parted, they sighed in unison and Matt slid once more against Taliesin’s chest, grinding the proof of his arousal against him. “Is it pretty?” he whispered, voice lilting upward as though trying to find just the right pitch. Soft palate, breathy.

 

It was all he could do not to have him right then, but Taliesin knew that Matt had to see. “You are,” he whispered against Matt’s ear; “you should go see.”

 

With a low sound of protest, Matt forced himself up on suddenly unsteady bare feet. He clasped both of Taliesin’s hands and led him to the bathroom to look. In the initial darkness, he couldn’t really tell the difference save for shading; same broad nose, same strong chin. Then Taliesin turned on the light and the world seemed to fall out from under him.

 

As though holding Matt up, Taliesin wrapped both arms around Matt’s waist, one hand pressed against his belly where the pajama pants had slid low while the other slipped inside to idly grasp Matt’s cock and stroke his palm along the hardness. “I told you,” he murmured against Matt’s ear, “It suits you.”

 

A moan unexpectedly closed Matt’s throat, but he forced himself to focus not on the waves of pleasure but on the carefully contoured cheekbones of his own face, the soft eyes that looked almost too big to be really his, and the plump pinkness of his own lips. “You’re amazing,” he gasped, his voice once more softening, not quite as feminine as it should be coming out of his new mouth but closer than before. “Thank you.”

 

Taliesin brushed a kiss on Matt’s ear and whispered; “It’s all you, darling. My pretty girl…”

 

Matt moaned again, and then let his voice rise to a gasp as the hand on his belly moved and Taliesin’s jeans thudded on the floor.

 

“You’re coming along beautifully,” Taliesin’s deep whisper continued as he gently thrust the thickness of his cock between Matt’s thighs, fully hard even before watching the shocked look on his lover’s face as he looked at a new self. “Wouldn’t you agree, darling?”

 

Matt pushed back into the sensation, crying out with delight when Taliesin’s grip tightened and the head of his thick cock slammed into Matt’s balls. “Yes…” he moaned, shuddering full bodied. He closed his eyes and for a moment he could almost feel it… feel Her.

 

“Open your eyes when I’m fucking you.” Taliesin’s voice was almost strong enough to be an order, but still a hard suggestion. “I want my girl to see what it looks like when a man desires her.”

 

It was almost too much, the hard thrusts between his clenched thighs mirrored with hard tug at his aching cock no match for the way his face - Her face, he thought in the heat of the moment - contorted with mounting need. “Fuck me…” he whispered, Her voice finally finding him in an innocent and soft cry somewhere between Allura’s certain tone and Cassandra’s youthful confusion. “Please…”

 

Taliesin’s hand gripped tighter and he began to feel the wetness spreading on his palm as Matt tipped over the edge, spreading his sticky seed against warm fleece. “Not yet.” Taliesin moaned, redoubling his efforts to tease with each hard thrust forcing Matt’s body against the sink’s pedestal. “I want to see you dressed… to see all of my pretty girl… before I take her virginity.”

 

That was enough to make Matt sob out loud, blushing dark and hot with what he knew should be shame but was definitely lust. He wanted to, he wanted to be Her in that moment and show his lover that deeply hidden side that nobody had ever seen. “Yes…” he moaned in Her voice. “Oh god yes.”

 

“Those pretty heels,” Taliesin moaned against Matt’s ear low and loud, his own wetness already spreading between Matt’s shaking thighs, “my fingers rubbing your clit under your pretty panties while I fuck you…”

 

Matt shuddered then and folded down the sticky front of his pajama pants. When Taliesin’s hands hooked on his hips, Matt braced himself against the sink and began to rub his fingers just the way he imagined - a large clit, wet and hard between his fingers but still desperately needy even after an orgasm. “Pretty just for you…” He gasped.

 

Grunting with each slowing thrust, Taliesin sighed; “Your pussy’s wet, isn’t it? All drippy and desperate like a good girl…”

 

“Yes…” Matt gasped, Her voice sticking in his throat. “I want you.”

 

“Good girl,” Taliesin held himself back, letting his precome streak Matt’s thighs with each push of his hips; “show me your pretty panties and I’ll reward my pretty lady.”

 

Twitching, Matt felt his cock throb unexpectedly hard. He was still tender from the first wave, but he was close to coming again as he heard Taliesin’s groan, fluid slicking his sac. It was more intense than he’d ever imagined, and watching his own face - seeing Taliesin’s unveiled lust behind him - only made it all the better. “Thank you… thank you so much…”

 

“On your knees, girl.”

 

Matt dropped without thinking, Taliesin’s hand sliding through his hair to turn him. He looked up at his lover only to be met with Taliesin’s slick cock sliding along his lips and pushing into his mouth.

 

“Clean it up while you rub your pussy.” Taliesin allowed himself to lean, free hand bracing himself on the sink as his legs threatened to give out. He couldn’t help himself, not when Matt looked so deliciously pretty. Watching the work he’d done smear was more than worth it.

 

With a moan, Matt’s throat opened and took him in, almost relieved with the familiar thrust along his tongue and pushing at the back of his throat. Focusing was tough, but he rubbed no less, he’d seen Marisha do it a hundred times, long fingers sliding over her velvety little clit until she was shaking even as she took care of one of them.

 

“God you’re fucking gorgeous.” Taliesin sighed, taking a tighter grip of Matt’s hair to push himself all the way in, liquid foundation and black eyeliner smudging on his thighs as Matt suckled at his dwindling manhood. The sensitivity took over quickly and Taliesin withdrew, turning his leg to let Matt rub his face on soft flesh as his body began to shake right where he knelt on the floor. “Such a pretty girl, my pretty girl.”

 

Matt gasped, and then whimpered, riding close to the edge but not quite there.

 

“Go ahead, sweetie,” Taliesin cooed. “Finger yourself for me.”

 

Cowed, but desperate, Matt opened his thighs wider and clung to Taliesin. It was easy to slide his fingers along the sticky mess of his balls and then press two fingers against the tightness of his hole. Part of him wondered if it would be like this again, this debauched heat that made him feel every bit the naive slut he’d only been in his imagination. They hadn’t even really talked about it… Taliesin had known exactly what he needed.

 

“Nice and deep,” Taliesin said calmly, “feel how wet and needy you are.”

 

He whimpered, and for a moment he could feel it. Tight and wet as he began to fuck himself with quick, hard thrusts of his fingers. It wasn’t the same as Taliesin’s cock or even the dildo he’d played with before another lover was in the picture, but in the moment it was exactly what he wanted.

 

“Just a little rub on your clit, it’s all swollen and needy, you’re about to explode aren’t you baby?”

 

It barely took that rub of his long fingers. Matt’s cock twitched against the linoleum floor when his fingertips caressed around the tender crown of his cockhead, a soft and inelegant cry was followed by deep gasps as he fingered himself through the orgasm, feeling himself tighten and throb.

 

And then there was silence for a long moment save for Matt’s eager breaths. Taliesin threaded his fingers in Matt’s hair, and then reached down to cup his cheek. The makeup had shockingly held up fairly well, smudged but fixable should he desire, but small tear tracks were easy to see in the bright bathroom light. “Come up here,” he whispered.

 

Matt nodded, unsurprised when Taliesin helped lift him and then met him with a gentle kiss that deepened fast.

 

“I love you,” Taliesin whispered, flushing hot when it was echoed; “so damn much. Like this, like anything… Matthew…”

 

Shaking arms wrapped around Taliesin’s chest, uncaring about the stickiness undoubtedly marring his shirt, and Matt buried his face in the crook of Taliesin’s neck, pressing small pink kisses there. He sniffed back the lump in his throat, but couldn't find words.

 

“You really are beautiful,” Taliesin whispered, stroking his hair. “I mean it.” When Matt looked back up, his sweet eyes shone with glossy wetness and he offered another gentle kiss. “And I’m honored to have a girlfriend like you.”


End file.
